- Singlet Oxygen Generation from a Water-Soluble Hypervalent Iodine(V) Reagent AIBX and H2O2: An Access to Artemisinin
-
Herein, we report an efficient method for the chemical generation of 1O2 by treatment of H2O2 with AIBX, a highly water-soluble, bench-stable, recyclable hypervalent iodine(V) reagent developed by our group. The generation of 1O2 was confirmed by the following results: (1) capture of 1O2 with the sodium salt of anthracene-9,10-bis(ethanesulfonate) produced the corresponding endoperoxide and (2) TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy) produced by the oxidation of 2,2,6,6-tetramethylpiperidine with 1O2 generated using the AIBX/H2O2 system was detected by electron spin resonance spectroscopy. To illustrate the potential utility of this method for organic synthesis, we used the AIBX/H2O2 system to perform typical reactions of 1O2: [2 + 2]/[4 + 2] cycloadditions, Schenck ene reactions, and heteroatom oxidation reactions, which afforded the corresponding products in high yields. Moreover, we used the method to synthesize the antimalarial drug artemisinin. Finally, we demonstrated that AIBX could be regenerated after the reaction by means of a workup involving extraction and removal of water to obtain a precursor of AIBX, which could then be re-oxidized.
- Hu, Ze-Nan,Shen, Hui-Jie,Zhang, Chi
-
supporting information
(2021/06/21)
-
- Discovery of a novel series of guanidinebenzoates as gut-restricted enteropeptidase and trypsin dual inhibitors for the treatment of metabolic syndrome
-
A novel series of guanidinebenzoate enteropeptidase and trypsin dual inhibitors has been discovered and SAR studies were conducted. Optimization was focused on improving properties for gut restriction, including increased aqueous solubility, lower cellular permeability, and reduced oral bioavailability. Lead compounds were identified with efficacy in a mouse fecal protein excretion study.
- Zhang, Xuqing,Zhu, Bin,Sun, Weimei,Wang, Mina,Albarazanji, Kamal,Ghosh, Brahma,Cummings, Maxwell,Lenhard, James,Leonard, James,Macielag, Mark,Lanter, James
-
supporting information
(2021/03/22)
-
- 5,8-DISUBSTITUTED-[1,2,4]TRIAZOLO[1,5-A]PYRIDINYL AND 5,8-DISUBSTITUTED-IMIDAZO[1,2-A]PYRIDINE DERIVATIVES USEFUL AS INHIBITORS OF ENTEROPEPTIDASE
-
The present invention is directed to 5,8-disubstituted-[1,2,4]triazolo[1,5- a]pyridinyl and 5,8-disubstituted-imidazo[1,2-a]pyridine derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by the enteropeptidase enzyme.
- -
-
Page/Page column 154
(2021/01/29)
-
- PARA-AMINO-BENZYL LINKERS, PROCESS FOR THEIR PREPARATION AND THEIR USE IN CONJUGATES
-
The present invention relates to para-amino-benzyl linker compounds useful for linking drug moieties to antibodies, to linker-drug compounds in which said para-amino-benzyl linker compounds are covalently linked to drug moieties, and to antibody-drug conjugates in which said para-amino-benzyl linker compounds are covalently linked to drug wherein said drug is enzymatically cleaved from the conjugate at a particular cell or tissue type targeted by said antibody.
- -
-
Page/Page column 93
(2021/11/26)
-
- Direct Intramolecular Aminoboration of Allenes
-
Direct intramolecular aminoboration of sulfonamidoallenes was realized using BCl3 as a boron source. The reactions benefited from the interaction between BCl3 and sulfonamides and provided a variety of borylvinyl heterocycles in good isolated yields. When chiral substrates were involved in the reactions, high stereoselectivity was observed, as can be ascertained by single-crystal X-ray diffraction experiments. Derivatization of the thus-obtained borylvinyl compounds proceeded readily, and different functionalities could be obtained via oxidation, halogenation, and Suzuki coupling reactions.
- Yang, Chun-Hua,Han, Meng,Li, Wenyan,Zhu, Ningning,Sun, Zhenzhen,Wang, Junjie,Yang, Zhantao,Li, Yue-Ming
-
supporting information
p. 5090 - 5093
(2020/07/15)
-
- IrIII-Catalyzed Selective ortho-Monoiodination of Benzoic Acids with Unbiased C?H Bonds
-
An iridium-catalyzed selective ortho-monoiodination of benzoic acids with two equivalent C?H bonds is presented. A wide range of electron-rich and electron-poor substrates undergo the reaction under mild conditions, with >20:1 mono/di selectivity. Importantly, the C?H iodination occurs selectively ortho to the carboxylic acid moiety in substrates bearing competing coordinating directing groups. The reaction is performed at room temperature and no inert atmosphere or exclusion of moisture is required. Mechanistic investigations revealed a substrate-dependent reversible C?H activation/protodemetalation step, a substrate-dependent turnover-limiting step, and the crucial role of the AgI additive in the deactivation of the iodination product towards further reaction.
- Weis, Erik,Johansson, Magnus J.,Martín-Matute, Belén
-
supporting information
p. 10185 - 10190
(2020/07/31)
-
- ANTI-EGFR ANTIBODY DRUG CONJUGATES
-
The invention relates to anti-Epidermal Growth Factor Receptor (EGFR) antibody drug conjugates (ADCs) which inhibit Bcl-xL, including compositions and methods of using said ADCs.
- -
-
Paragraph 1151
(2019/06/07)
-
- Pd-Catalyzed Selective Synthesis of Cyclic Sulfonamides and Sulfinamides Using K2S2O5 as a Sulfur Dioxide Surrogate
-
A variety of cyclic sulfonamides and sulfinamides could be selectively synthesized under Pd catalysis using haloarenes bearing amino groups and a sulfur dioxide (SO2) surrogate. The amount of base was key in determining the selectivity. Mechanistic studies revealed that sulfinamides were initially formed via an unprecedented formal insertion of sulfur monoxide and were oxidized to sulfonamides in the presence of an iodide ion and DMSO.
- Konishi, Hideyuki,Tanaka, Hiromichi,Manabe, Kei
-
supporting information
p. 1578 - 1581
(2017/04/13)
-
- ANTI-CD98 ANTIBODIES AND ANTIBODY DRUG CONJUGATES
-
The invention relates to anti-CD98 antibodies and antibody drug conjugates (ADCs), including compositions and methods of using said antibodies and ADCs.
- -
-
Page/Page column 477-478
(2018/01/15)
-
- ANTI-EGFR ANTIBODY DRUG CONJUGATES
-
The invention relates to anti-Epidermal Growth Factor Receptor (EGFR) antibody drug conjugates (ADCs) which inhibit Bcl-xL, including compositions and methods of using said ADCs.
- -
-
Page/Page column 426
(2018/01/15)
-
- ANTI-CD98 ANTIBODIES AND ANTIBODY DRUG CONJUGATES
-
The invention relates to anti-CD98 antibodies and antibody drug conjugates (ADCs), including compositions and methods of using said antibodies and ADCs.
- -
-
Page/Page column 625
(2018/01/17)
-
- ANTI-CD98 ANTIBODIES AND ANTIBODY DRUG CONJUGATES
-
The invention relates to anti-CD98 antibodies and antibody drug conjugates (ADCs), including compositions and methods of using said antibodies and ADCs.
- -
-
Page/Page column 367
(2018/01/15)
-
- ANTI-B7-H3 ANTIBODIES AND ANTIBODY DRUG CONJUGATES
-
The invention relates to B7 homology 3 protein (B7-H3) antibodies and antibody drug conjugates (ADCs), including compositions and methods of using said antibodies and ADCs.
- -
-
Paragraph 2093; 2150
(2018/01/13)
-
- BCL-XL Inhibitory Compounds and Antibody Drug Conjugates Including the Same
-
Small molecule Bcl-xL inhibitors and Antibody Drug Conjugates (ADCs) comprising small molecule Bcl-xL inhibitors are disclosed herein. The Bcl-xL inhibitors and ADCs of the disclosure are useful for, among other things, inhibiting anti-apoptotic Bcl-xL proteins as a therapeutic approach towards the treatment of diseases that involve a dysregulated apoptosis pathway.
- -
-
Paragraph 106
(2016/06/28)
-
- BCL XL INHIBITORY COMPOUNDS HAVING LOW CELL PERMEABILITY AND ANTIBODY DRUG CONJUGATES INCLUDING THE SAME
-
The present disclosure concerns Bcl-xL inhibitors having low cell permeability, antibody drug conjugates (ADCs) comprising the inhibitors, synthons useful for synthesizing the ADCs, compositions comprising the inhibitors or ADCs, and various methods of using the inhibitors and ADCs.
- -
-
Paragraph 0001171
(2016/07/05)
-
- Design, synthesis, structure, and dehydrogenation reactivity of a water soluble o-iodoxybenzoic acid derivative bearing a trimethylammonium group
-
5-Trimethylammonio-1, 3-dioxo-1, 3-dihydro-1λ5-benzo[d][1, 2]iodoxol-1-ol anion (AIBX 1a), an o-iodoxybenzoic acid (IBX) derivative having the trimethylammonium moiety on its phenyl ring, possesses very good solubility in water and distinct oxidative properties from IBX, which is demonstrated in the oxidation of various β-keto esters to the corresponding dehydrogenated products using water as cosolvent. The regeneration of AIBX 1a can be easily realized from the reaction mixture due to its good water solubility.2011 American Chemical Society.
- Cui, Li-Qian,Dong, Zhi-Lei,Liu, Kai,Zhang, Chi
-
supporting information; experimental part
p. 6488 - 6491
(2012/02/02)
-
- Design and SAR of selective T-type calcium channel antagonists containing a biaryl sulfonamide core
-
T-type calcium channel antagonists were designed using a protocol involving the program SPROUT and constrained by a ComFA-based pharmacophore model. Scaffolds generated by SPROUT were evaluated based on their ability to be translated into structures that were synthetically tractable. From this exercise, a novel series of potent and selective T-type channel antagonists containing a biaryl sulfonamide core were discovered.
- Hangeland, Jon J.,Cheney, Daniel L.,Friends, Todd J.,Swartz, Stephen,Levesque, Paul C.,Rich, Adam J.,Sun, Lucy,Bridal, Terry R.,Adam, Leonard P.,Normandin, Diane E.,Murugesan, Natesan,Ewing, William R.
-
p. 474 - 478
(2008/09/18)
-
- HYDRAZONE DERIVATIVE
-
A compound represented by the following formula (I): wherein R1 represents hydrogen, aryl which may have a substituent, a saturated or unsaturated 5- to 7-membered heterocyclic group which may have a substituent, etc.; R2 represents hydrogen, aryl which may have a substituent, a saturated or unsaturated 5- to 7-membered heterocyclic group which may have a substituent, etc.; R3 represents hydrogen, etc.; Ar represents a divalent group derived from aromatic hydrocarbon, etc.; X represents a single bond, linear or branched alkylene having from 1 to 3 carbon atoms which may have a substituent, etc.; and G represents halogen, a saturated or unsaturated 5- or 6-membered cyclic hydrocarbon group which may have a substituent, a saturated or unsaturated 5- to 7-membered heterocyclic group which may have a substituent, etc., a salt thereof or a solvate thereof; and an agent for inhibiting aggregation and/or deposition of an amyloid protein or an amyloid-like protein, which comprises the compound, a salt thereof or a solvate thereof
- -
-
Page/Page column 48
(2010/11/08)
-
- NPY-5 antagonists
-
The present invention provides NPY-5 receptor antagonists having a Formula (I) Methods and pharmaceutical compositions useful for treating diseases, conditions and/or disorders modulated by the above NPY-5 receptor antagonists are also provided.
- -
-
-
- Synthesis of novel iodo derived bicalutamide analogs
-
A series of optically active nonsteroidal selective androgen receptor modulators with structures analogous to bicalutamide was prepared by replacing the trifluoromethyl group with iodine and the sulfonyl linker by oxygen.
- Nair, Vipin A.,Mustafa, Suni M.,Mohler, Michael L.,Fisher, Scott J.,Dalton, James T.,Miller, Duane D.
-
p. 9475 - 9477
(2007/10/03)
-
- Design, synthesis, and pharmacological characterization of 4-[4,4-Dimethyl-3-(4-hydroxybutyl)-5-oxo-2-thioxo-1-imidazolidinyl]-2-iodoben zonitrile as a high-affinity nonsteroidal androgen receptor ligand
-
4-[4,4-Dimethyl-3-(4-hydroxybutyl)-5-oxo-2-thioxo-1-imidazolidinyl]-2-trifluo romethylbenzonitrile (RU 59063) is a prototype of a new class of high-affinity nonsteroidal androgen receptor (AR) ligands. The search for a radioiodinated AR ligand prompted us
- Van Dort,Robins,Wayburn
-
p. 3344 - 3347
(2007/10/03)
-
- Fungicidal acylamidobenzamides
-
Fungicidal compounds having the formula (I): in which D and E are independently H or F; X and Y are 0 or S; R1 to R4 have various specified values; A and B are independently H, iodo, nitro, cyano, C1 4 alkoxycarbonyl, Csu
- -
-
-
- SYNTHESIS OF 4-(N-ACETYL-L-TYROSYL)AMINO-2-IODOBENZOIC ACID
-
The title compound was prepared by a three-step synthesis from diacetyltyrosine (XV) and 4-amino-2-iodobenzoic acid (I).Syntheses of acid I and 4-amino-3-iodobenzoic acid (II) have been revised and modified. 1H and 13C NMR spectra of the synthesized compo
- Protiva, Jiri,Krecek, Vaclav,Maca, Bohumil,Urban, Jiri,Budesinsky, Milos,Prochazka, Milos
-
p. 1012 - 1018
(2007/10/02)
-